Potassium Carbonate → 4-(3-Chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

HRID 555877Notes

Reaction equation

HRID 555877 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:20](Cl)=[N:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:14][C:15]1[C:20]([O:1][C:2]2[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=2)=[N:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 113897574-Hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 593513464-(3-Chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxy-N-methoxy-N-methylbenzamide (6.50 g, 35.9 mmol), 2,3-dichloropyrazine (6.95 g, 46.6 mmol), and potassium carbonate (12.40 g, 90 mmol) in acetonitrile (70 mL) was heated at reflux in 18 h. The reaction mixture was cooled, concentrated, taken up in H2O, extracted with EtOAc, dried over MgSO4, concentrated and purified by ISCO (50% EtOAc/Hexanes) to give the titled compound. MS [M+1]: 294.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in 18 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by ISCO (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-571f4b185adb4d8d9761762bbe24846a
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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